EP1141138B1 - Colorants azoiques de phtalimidyle, leur procede de preparation et leur utilisation - Google Patents

Colorants azoiques de phtalimidyle, leur procede de preparation et leur utilisation Download PDF

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Publication number
EP1141138B1
EP1141138B1 EP99965559A EP99965559A EP1141138B1 EP 1141138 B1 EP1141138 B1 EP 1141138B1 EP 99965559 A EP99965559 A EP 99965559A EP 99965559 A EP99965559 A EP 99965559A EP 1141138 B1 EP1141138 B1 EP 1141138B1
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Prior art keywords
formula
dye
hydrogen
cyano
alkyl
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German (de)
English (en)
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EP1141138A1 (fr
Inventor
Urs Lauk
Antoine Clement
Romeo Dreier
Alfons Arquint
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Huntsman Advanced Materials Switzerland GmbH
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Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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Priority to DK99965559T priority patent/DK1141138T3/da
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
    • C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
    • C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber

Definitions

  • the present invention relates to disperse dyes with an N-alkyl phthalimide diazo component and an aniline coupling component, manufacturing method of these dyes and their use for dyeing or printing fiber materials, especially polyester-containing fiber materials.
  • Dispersion azo dyes with an N-alkyl-phthalimide diazo component and an aniline coupling component have long been known and are used for dyeing hydrophobic Fiber materials used.
  • EP-A 0 443 984 describes cyano-substituted N-alkylphthalmide azo dyes described, the polyesters violet or red colors with good thermal migration to lend.
  • the present invention thus relates to disperse dyes which are very washable Sweat-resistant dyeings result, and also both in the exhaust and thermosol process as well as in textile printing have a good ability to build up.
  • the dyes are too suitable for etching printing.
  • the dyes according to the invention correspond to the formula wherein R is methyl, R 1 is hydrogen, halogen, cyano or nitro, R 2 is bromine or cyano, R 3 is hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, R 4 is -NHCOR 7 where R 7 is ethyl or methyl, R 5 is unsubstituted or by hydroxy, cyano, acyloxy, or phenyloxy substituted C 1 -C 6 alkyl, where x is a number from 0 to 4, and the alkyl chain from C 2 can optionally be interrupted by one or more oxygen atoms, or a radical of the formula -CH 2 CH 2 -O-COR 8 or the formula means, and R 6 is a radical of the formula means, where R 8 and R 9 are independently C 1 -C 4 alkyl and R 10 is hydrogen or C 1 -C 4 alkyl.
  • R 1 as halogen is, for example, fluorine, chlorine or bromine, in particular chlorine or bromine, especially bromine.
  • R 3 as halogen is, for example, fluorine, chlorine or bromine, especially chlorine or bromine, especially chlorine.
  • R 3 as C 1 -C 4 alkoxy is, for example, methoxy, ethoxy, straight-chain or branched propoxy or straight-chain or branched butoxy. Ethoxy or in particular methoxy are preferred.
  • acyloxy in R 5 in particular propionyloxy or especially acetyloxy comes into question.
  • x 2 or in particular 1.
  • R 5 as a substituted C 1 -C 6 alkyl is in particular a C 1 -C 4 alkyl substituted by cyano, especially a cyanoethyl.
  • R 1 is hydrogen, bromine or cyano, especially hydrogen or bromine.
  • Bromine is particularly preferred as R 2 .
  • Hydrogen is particularly preferred as R 3 .
  • R 5 is particularly preferably ethyl or cyanoethyl.
  • the radical -CH (CH 3 ) -COOC 2 H 5 is very particularly preferred as R 6 .
  • R 1 R 2 R 3 R 4 R 5 R 6 100 -H Br -H -NHCOCH 3 -C 2 H 5 -CH (CH 3 ) COOC 2 H 5 101 -H Br -H -NHCOC 2 H 5 -C 2 H 5 -CH 2 COOCH 3 102 -H Br -H -NHCOCH 3 -C 2 H 5 -CH 2 COOC 2 H 5 103 -H Br -H -NHCOC 2 H 5 -C 2 H 5 -CH (CH 3 ) COOCH 3 104 -H Br -H -NHCOCH 3 -C 2 H 5 -CH 2 COOCH 3 105 -H Br -H -NHCOC 2 H 5 -C 2 H 5 -CH 2 COOC 2 H 5 106 -H Br -H -NHCOCH 3 -C 2 H 5 -CH (CH 3 ) COOCH 3 107 -H Br -H -NHCOCH 3 -C 2 H
  • Another object of the present invention is the method of manufacture the dyes of the formula (1) according to the invention.
  • the intermediate product of formula (51) is nitrated or acidified once or several times in an acidic environment by generally known methods, the halogen substituents optionally being able to be replaced by cyano by methods which are also known, and then diazotized and onto a compound of the formula wherein R 3 , R 4 , R 5 and R 6 have the meanings and preferences mentioned above.
  • the halogenation is e.g. executed so that the compound of formula (51) is first in acetic acid with sodium acetate, and then in the same medium with bromine Mono or dibromo compound.
  • the compound of formula (51) is also diazotized in a manner known per se, e.g. with sodium nitrite in acid, e.g. hydrochloric acid or sulfuric acid, aqueous medium.
  • diazotization can also be carried out with other diazotizing agents, e.g. with nitrosylsulfuric acid be carried out.
  • An additional acid can be present in the reaction medium during diazotization be present, e.g. Phosphoric acid, sulfuric acid, acetic acid, propionic acid, Hydrochloric acid or mixtures of these acids, e.g. Mixtures of propionic acid and Acetic acid.
  • the diazotization is expedient at temperatures from -10 to 30 ° C, e.g. from -10 ° C to room temperature.
  • the coupling of the diazotized compound of formula (51) to the coupling component of the formula (52) is also carried out in a known manner, for example in acidic, aqueous or aqueous-organic medium, advantageously at temperatures from -10 to 30 ° C, in particular below 10 ° C.
  • the acids used are e.g. Hydrochloric acid, acetic acid, propionic acid, Sulfuric acid or phosphoric acid.
  • the diazo components of the formula (51) and the coupling components of the formula (52) are known or can be produced in a manner known per se.
  • the dyes according to the invention can be used as dyes for dyeing and printing semi-synthetic and in particular synthetic hydrophobic fiber materials, especially textile materials. Textile materials from blended fabrics which contain such semi-synthetic or synthetic hydrophobic fiber materials can also be dyed or printed with the aid of the compounds according to the invention. Cellulose 21 ⁇ 2-acetate and cellulose triacetate are particularly suitable as semi-synthetic fiber materials.
  • Synthetic hydrophobic fiber materials consist mainly of linear, aromatic Polyesters, for example those made from terephthalic acid and glycols, especially ethylene glycol or condensation products from terephthalic acid and 1,4-bis (hydroxymethyl) cyclohexane; from polycarbonates, e.g. those from ⁇ , ⁇ -dimethyl-4,4-dihydroxy-diphenylmethane and phosgene, from fibers based on polyvinyl chloride and polyamide.
  • polyesters for example those made from terephthalic acid and glycols, especially ethylene glycol or condensation products from terephthalic acid and 1,4-bis (hydroxymethyl) cyclohexane; from polycarbonates, e.g. those from ⁇ , ⁇ -dimethyl-4,4-dihydroxy-diphenylmethane and phosgene, from fibers based on polyvinyl chloride and polyamide.
  • polyester fiber materials are dyed using the exhaust process from aqueous dispersion in the presence of conventional anionic or non-ionic Dispersants and optionally conventional swelling agents (carriers) at temperatures between 80 and 140 ° C.
  • Cellulose-21 ⁇ 2-acetate is preferably dyed between 65 to 85 ° C and cellulose triacetate at temperatures between 65 and 115 ° C.
  • the dyestuffs according to the invention do not dye wool or cotton present at the same time in the dye bath, or only do so slightly (very good reserve), so that they can also be used well for dyeing polyester / wool and polyester / cellulose fiber blended fabrics.
  • the dyes according to the invention are suitable for dyeing by the thermosol process, in the exhaust process and for printing processes.
  • the fiber materials mentioned can be in the various processing forms are present, e.g. as fiber, thread or fleece, as woven or knitted fabric.
  • the dyes of the invention are converted into a dye preparation before using them to convict.
  • the dye is ground so that its particle size averages between 0.1 and 10 microns. Grinding can be carried out in the presence of dispersants respectively.
  • the dried dye with a dispersant ground or kneaded in paste form with a dispersant and then in vacuo or dried by atomization With the preparations obtained in this way, Add water to make pastes and dye baths.
  • the usual thickeners will be used for printing, e.g. modified or unmodified natural products, for example alginates, British gum, gum arabic, Crystal gum, locust bean gum, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, Starch or synthetic products, for example polyacrylamides, polyacrylic acid or their copolymers or polyvinyl alcohols.
  • modified or unmodified natural products for example alginates, British gum, gum arabic, Crystal gum, locust bean gum, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, Starch or synthetic products, for example polyacrylamides, polyacrylic acid or their copolymers or polyvinyl alcohols.
  • the dyes according to the invention give the materials mentioned, especially the polyester materials, level shades of very good fastness properties, especially good ones Lightfastness, heat setting, pleating, chlorine and wet fastness such as water, sweat and Wash fastness; the colorations are also characterized by very good rub fastness. Particularly noteworthy are the good perspiration and especially wash fastness of the dyeings obtained.
  • the dyes according to the invention can also be used well for the production of Mixed shades together with other dyes.
  • the dyes according to the invention are also well suited for dyeing hydrophobic fiber materials from supercritical CO 2 .
  • the above-mentioned use of the dyes according to the invention is also an object of the present invention, as is a method for dyeing or printing semi-synthetic or synthetic hydrophobic fiber materials, in particular textile materials, which consists in applying a dye according to the invention to the materials mentioned or incorporating them into them.
  • the hydrophobic fiber materials mentioned are preferably textile polyester materials. Further substrates which can be treated by the process according to the invention and preferred process conditions can be found above in the detailed explanation of the use of the dyes according to the invention.
  • the invention further relates to the hydrophobic fiber materials, preferably polyester textile materials, dyed or printed by the process mentioned.
  • the dyes according to the invention are also suitable for modern recording methods, such as thermal transfer printing.
  • the following examples serve to illustrate the invention. Unless otherwise stated, the parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius. The relationship between parts by weight and parts by volume is the same as that between grams and cubic centimeters.
  • the fully reacted mixture is mixed with 8.00 g of ice water within 10 minutes and then to a mixture consisting of 25.20 g of glacial acetic acid, 2.32 g of a 32% hydrochloric acid, 80.00 g of ice water and 20.60 g of one 31.1% aqueous solution of the compound of formula added dropwise within 40 minutes at a pH of approx. 2.5 and a temperature of 0-5 ° C. and stirred for 40 minutes. Thereafter, 29.00 g of a 15% strength aqueous sodium hydroxide solution are added dropwise at a temperature of 0-5 ° C. over the course of 40 minutes, the mixture is brought to a pH of 1.0 and the mixture is stirred for a further 15 minutes. The resulting red suspension is filtered off with 250 g of deionized water. washed and dried to a pH> 5. 9.83 g of the dye of the formula are obtained which polyester dyes in a brilliant red shade.
  • the fully reacted mixture is then within 10 minutes to a mixture consisting of 6.30 g of glacial acetic acid, 0.58 g of a 32% hydrochloric acid, 11.00 g of ice water and 5.20 g of a 31.1% aqueous solution added dropwise to the compound of formula (54) at a temperature of 0-5 ° C and stirred for 120 minutes. Then 15.00 g of ice water are added dropwise within 10 minutes, the resulting red suspension is filtered off with deionized water. washed and dried. 2.10 g of the dye of the formula are obtained which polyester dyes in a reddish brown tone.
  • 1 part by weight of the dye of the formula is ground together with 17 parts by weight of water and 2 parts by weight of a commercially available disperser of the dinaphthylmethane disulfonate type in a sand mill and converted into a 5% aqueous dispersion.
  • a 1% colouration (based on dye and substrate) on polyester fabric is created and reductively cleaned in a high-temperature exhaust process at 130 ° C.
  • the dyeing obtained in this way has very good fastness properties, in particular excellent fastness to washing.
  • polyester fabric is used in the thermosol process is dyed (10g / l dye, liquor absorption 50%, fixing temperature 210 ° C).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Paper (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Paints Or Removers (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)

Claims (14)

  1. Colorants de formule
    Figure 00220001
    dans laquelle
    R est le groupe méthyle, R1 est un atome d'hydrogène ou d'halogène ou un groupe cyano ou nitro, R2 est le brome ou le groupe cyano, R3 est un atome d'hydrogène ou d'halogène ou un groupe alkyle en C1 à C4 ou alcoxy en C1 à C4, R4 est -NHCOR7 où R7 est le groupe éthyle ou méthyle, R5 est un groupe alkyle en C1 à C6 non substitué ou substitué par hydroxy, cyano, acyloxy,
    Figure 00220002
    ou phényloxy, x étant un nombre de 0 à 4, et la chaíne alkyle à partir de C2 pouvant éventuellement être interrompue par un ou plusieurs atomes d'oxygène,
    ou encore un radical de formule -CH2CH2-O-COR8, de formule
    Figure 00220003
    ou de formule
    Figure 00220004
    et R6 est un radical de formule
    Figure 00220005
    R8 et R9 représentant chacun indépendamment de l'autre un groupe alkyle en C1 à C4, et R10 étant un atome d'hydrogène ou un groupe alkyle en C1 à C4.
  2. Colorants selon la revendication 1, dans laquelle R1 est un atome d'hydrogène ou de brome ou le groupe cyano.
  3. Colorants selon l'une des revendications 1 et 2, dans lesquelles R3 est un atome d'hydrogène.
  4. Colorants selon l'une des revendications 1 à 3, dans lesquelles R5 est le groupe éthyle ou cyanoéthyle.
  5. Colorants selon la revendication 1, dans laquelle R8 est le radical -CH(CH3)COOC2H5.
  6. Colorant selon la revendication 1, de formule
    Figure 00230001
  7. Colorant selon la revendication 1, de formule
    Figure 00230002
  8. Colorant selon la revendication 1, de formule
    Figure 00230003
  9. Colorant selon la revendication 1, de formule
    Figure 00240001
  10. Colorant selon la revendication 1, de formule
    Figure 00240002
  11. Procédé de préparation des colorants de formule 1 selon la revendication 1, caractérisé en ce qu'on soumet à une nitration un phtalimide de formule
    Figure 00240003
    en milieu acide, puis on alkyle le composé nitro obtenu et, par un traitement par réduction, on le convertit en un produit intermédiaire de formule
    Figure 00240004
    on nitre le produit intermédiaire de formule (51) en milieu acide, ou encore on l'halogène une ou plusieurs fois, les substituants halogéno pouvant éventuellement être remplacés par des groupes cyano, puis on procède à une diazotation, puis à une copulation sur un composé de formule
    Figure 00250001
    dans laquelle R1, R3, R4, R5 et R6 ont les significations données à propos de la formule (1).
  12. Procédé pour teindre ou imprimer des matériaux fibreux hydrophobes semi-synthétiques ou synthétiques, en particulier des matériaux textiles, caractérisé en ce qu'on applique un colorant de formule (1) selon la revendication 1 sur les matériaux mentionnés, ou encore on l'y incorpore.
  13. Utilisation des colorants de formule (1) selon la revendication 1 pour teindre ou imprimer des matériaux textiles contenant des polyesters.
  14. Les matériaux fibreux hydrophobes teints ou imprimés par le procédé selon la revendication 12, en particulier des matériaux textiles contenant des polyesters.
EP99965559A 1998-12-31 1999-12-27 Colorants azoiques de phtalimidyle, leur procede de preparation et leur utilisation Expired - Lifetime EP1141138B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP99965559A EP1141138B1 (fr) 1998-12-31 1999-12-27 Colorants azoiques de phtalimidyle, leur procede de preparation et leur utilisation
DK99965559T DK1141138T3 (da) 1998-12-31 1999-12-27 Phthalimidylazopigmenter, fremgangsmåde til fremstilling haraf og deres anvendelse

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP98124859 1998-12-31
EP98124859 1998-12-31
EP99965559A EP1141138B1 (fr) 1998-12-31 1999-12-27 Colorants azoiques de phtalimidyle, leur procede de preparation et leur utilisation
PCT/EP1999/010396 WO2000040656A1 (fr) 1998-12-31 1999-12-27 Colorants azoiques de phtalimidyle, leur procede de preparation et leur utilisation

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Publication Number Publication Date
EP1141138A1 EP1141138A1 (fr) 2001-10-10
EP1141138B1 true EP1141138B1 (fr) 2004-09-15

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US (1) US6555664B1 (fr)
EP (1) EP1141138B1 (fr)
JP (1) JP5031945B2 (fr)
KR (1) KR100674493B1 (fr)
CN (1) CN1326945C (fr)
AT (1) ATE276319T1 (fr)
AU (1) AU2102800A (fr)
DE (1) DE59910538D1 (fr)
DK (1) DK1141138T3 (fr)
ES (1) ES2228159T3 (fr)
TW (1) TWI243192B (fr)
WO (1) WO2000040656A1 (fr)

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CN105566940A (zh) * 2016-01-27 2016-05-11 杭州福莱蒽特精细化工有限公司 一种邻苯二甲酰亚胺偶氮染料及其制备方法和应用
CN105566939B (zh) * 2016-01-28 2018-03-30 俞杏英 一种橙色分散染料单体化合物及其制备方法和应用
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CN105733291B (zh) * 2016-01-28 2018-03-30 俞杏英 一种高移染红色分散染料单体化合物及其制备方法和应用
TWI707002B (zh) 2016-05-25 2020-10-11 瑞士商杭斯曼高級材料公司 分散偶氮染料、其製備方法及其用途
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TW328094B (en) * 1994-02-11 1998-03-11 Ciba Sc Holding Ag Phthalimidylazo dyes, process for their preparation and the use thereof
US6008332A (en) * 1994-02-11 1999-12-28 Ciba Specialty Chemicals Corporation Phthalimidylazo dyes, process for their preparation and the use thereof

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DE59910538D1 (de) 2004-10-21
CN1326945C (zh) 2007-07-18
ES2228159T3 (es) 2005-04-01
KR100674493B1 (ko) 2007-02-05
KR20010100016A (ko) 2001-11-09
DK1141138T3 (da) 2004-12-06
CN1331730A (zh) 2002-01-16
TWI243192B (en) 2005-11-11
AU2102800A (en) 2000-07-24
JP2002534551A (ja) 2002-10-15
JP5031945B2 (ja) 2012-09-26
WO2000040656A1 (fr) 2000-07-13
ATE276319T1 (de) 2004-10-15
EP1141138A1 (fr) 2001-10-10
US6555664B1 (en) 2003-04-29

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